title: Chemical synthesis of β-arabinofuranosyl containing oligosaccharides derived from plant cell wall extensins.
abstract: Extensins are plant-derived glycoproteins that are densely modified by oligo-arabinofuranosides linked to hydroxyproline residues. These glycoproteins have been implicated in many aspects of plant growth and development. Here, we describe the chemical synthesis of a tetrameric β(1-2)-linked arabinofuranoside that is capped by an α(1-3)-arabinofuranoside and a similar trisaccharide lacking the capping moiety. The challenging β(1-2)-linked arabinofuranosides were installed by using an arabinofuranosyl donor protected with 3,5-O-(di-tert-butylsilane) and a C-2 2-methylnaphthyl (Nap) ether. It was found that the cyclic silane-protecting group of the glycosyl donor greatly increased β-anomeric selectivity. It was, however, imperative to remove the silane-protecting group of an arabinosyl acceptor to achieve optimal anomeric selectivities. The anomeric linker of the synthetic compounds was modified by a biotin moiety for immobilization of the compounds to microtiter plates coated with streptavidine. The resulting microtiter plates were employed to screen for binding against a panel of antibodies elicited against plant cell wall polysaccharides.
authors.affiliation: Complex Carbohydrate Research Center, The University of Georgia, 315 Riverbend Road, Athens, GA 30602, USA.
authors.forename: Sophon
authors.initials: S
authors.lastname: Kaeothip
authors.forename: Geert-Jan
authors.initials: GJ
authors.lastname: Boons
mesh_terms: D001087:Arabinonucleosides / Q000737:chemistry*; D002473:Cell Wall / Q000737:chemistry*; D006023:Glycoproteins / Q000737:chemistry*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010940:Plant Proteins / Q000737:chemistry*; D010944:Plants / Q000737:chemistry*
chemical_list: D001087:Arabinonucleosides; D006023:Glycoproteins; D009844:Oligosaccharides; D010940:Plant Proteins; C005488:extensin protein, plant